“So, tell me again, what do you do for a living?”

“I’m a lawyer.” The woman replied

“Age?”

“I am 35 years old.”

“Just for the record, for our viewers, why are you here with us today?” i strapped both her arms above her head before pulling the rope to create some discomfort by straining her shoulders.

“I came here to be sexually degraded and humiliated” she replied

She looked extremely beautiful and for sure she looked a lot younger than 35 years. She was tall with very long legs complemented with very fit and sporty body. Certainly, most people would consider her sexy as hell. She was wearing tight black dress just over the knees paired with black lace high heels. According to the information she gave us in advance, she had worn this dress on a few very important cases in court she had won during the last 4-5 years. In the most recent case, she told us, she had defended famous mobster, helping him to evade some serious charges. Of course, she was paid extremely well for the job.

“I think your dress is wet.” I touched her between her tights. “And your legs are wet as well. Why is that” I asked her

“I peed myself.” her voice was trembling a bit

“How so?” I insisted

“You told me to.” She almost whispered it

“Now we will also tie your legs” I took a pair of scissors and started cutting the wet fabric of the dress. I made two cuts, one on the front, just over her belly button and one behind, just over her ass. Having divided the bottom part of the dress in two pieces, I easily spread her legs, strapping them with two belts anchored to the ground. Her legs were really long and it seemed that she was still standing comfortable in her heels, that’s why I adjusted the position of the belts stretching the ropes to the maximum, forcing her in a bit more stretched and uncomfortable position.

It was time for her panties. As a refined and accurate woman she had chosen black color for the panties. Anyway, the color wasn’t important. I cut them exposing her genitalia to everybody. It was hardly surprising that her cunt seemed in good condition. It definitely looked like an used hole, but it was still tight. Nevertheless she had shaven it very carefully for the occasion.

“Why is your cunt wet?” I gently ran my fingers in her list.

“Because it turns me on to be humiliated and used as a cock sleeve”

“Don’t worry, you will like it here. I can see your cunt has been well used over the years but can you point out for our viewers how many cocks have you had in your asshole”

“Only 3 or 4 times”

“Do you consider that satisfying?”

“No, sir, I need to be fucked in the ass”.

I didn’t wait her to finish her sentence and opened the bag with the groceries we have asked her to bring. I took the biggest cucumber I found – a wonderful 12.5 inch result result of the modern agriculture. The thickness of the vegetable wasn’t bad either, as it was almost 2 inches in diameter. Using her own cunt juice for lubrication I inserted it slowly in her asshole.

“Do you know what is happening right now?” I moved behind her still holding the cucumber because her rectum was now battling to expel the intruder.

“I have a giant cucumber buried in my asshole and I can’t wait to feel it even deeper” she declared looking at the cameras

I didn’t make her wait and I started fucking her asshole with the green phallus. I was a bit more gentle in the beginning but after a while I started thrusting harder making her moan. She must have been really horny already because only after few minutes of penetration she had an anal orgasm. Her body started shaking in convulsions and a second later she squirted. The burst of pee bathed her long legs for a second time this evening and even sprayed the camera which was on the ground underneath her cunt.

I loosened my grip on the cucumber, letting her clenching rectum to slowly expel the giant vegetable. Once it was completely out, I rubbed the dirty phallus against her wet cunt. Her reaction was what I already expected.

“Please fuck me more” she moaned.

“You can count on that, slut.” I smiled at her depravity. “Now we will check how deep your morals can go”.

The moment I said that an automatic sex machine was positioned underneath her. I installed the biggest dildo available – a large 15 inch ribbed monster, 2.8 inch in diameter. I took the remote control but before I hit the start button I had to ask her one more thing.

“How do you want your payment cunt? Is cash fine?”

She only nodded in confirmation and I started the machine. As starters I programmed it to go very slowly to build some additional anticipation for her so it took almost a minute before the enormous head of the dildo pressed against her well prepared sphincter.

“You will get paid for every 5 inches” I informed her

I wanted her to feel everything, so I didn’t increase the speed. The head went through her sphincter with almost no resistance. The dildo continued its way upward slowly stretching her bowels until it hit its first 5 inches. The buzzing sound from the fucking machine stopped. During the pause I waved under her nose the first small wad of money she earned and left them before leaving them on the nearby table.

“I am sure you are accustomed to earn a lot more” I said and I hit the start button again. The ribbed plastic phallus continued its way through her bowels. I looked at her face. I could see that she was experiencing some pain from the brutal stretching of her rich lawyer ass, but soon her moans convinced me that she was enjoying it. I was glad that the cameras were capturing everything. When the dildo hit the 10 inch mark I left another wad of money on the table for her. The last 5 inches were really difficult for her body to accept but the machine didn’t care at all. Soon the whole length of the monster disappeared inside as her anal impalement has reached its deepest point.

“Impressive accomplishment” I left the last part of the payment on the table. “I don’t know if the next few hours will be fun for you, but you will get the bonus if you last. The money on the table are already yours”. I took the money rolls from the table and quickly filled her front cunt with them. She looked confused. I took some black tape and sealed her hole with it. After all I didn’t want her to drop the money she had earned.

While putting the tape I couldn’t help but notice a bulge just above her naval. For now it was not so obvious because it was underneath the black dress so I decided to make things even more interesting for the viewers. I ripped her dress completely revealing her beautiful body and the giant deformation on her abdomen caused by the brutal impalement. I started the fucking machine. I stood there for a while observing the convulsions of her rich lawyer’s body as she was receiving the deepest anal penetration in her life. Despite the initial discomfort, her excitement grew, and I saw her experience another strong orgasm. Once her orgasm finished, I put the piston of the machine on its highest speed. She immediately realised that nobody will stop the fucking machine as the enormous phallus continued pistoning through her ravaged colon. She tried to fight but the restraints didn’t let her, her desperate movements only made the view for the cameras more interesting.

...

I came back a few hours later. She was unconscious and her body was hanging in the ropes. The machine has already stopped as it was programmed to go for only 4 hours. The ribbed monster was now only halfway buried in her as her asshole was partially prolapsing around the monster. Her overstretched and swollen sphincter had failed from the brutal penetration it had received for hours. I think she will be happy with the results. After all her payment was waiting for her in her own cunt.